


Firsts - Sam

by reggie



Series: Firsts 'verse [2]
Category: Supernatural
Genre: F/M, First Time, Het and Slash, Loss of Virginity, M/M
Language: English
Status: Completed
Published: 2013-08-27
Updated: 2013-08-27
Packaged: 2017-12-24 20:25:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,279
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/944276
Author URL: https://archiveofourown.org/users/reggie/pseuds/reggie
Summary: <blockquote class="userstuff">
              <p>This is part two of Firsts 'verse chronicling the Winchester boys' first sexual encounters. This chapter deals with Sam's first times. The first in the series was Dean's and the third will be Wincest but each fic is stand-alone.</p><p>Sam wasn’t very experienced because he wasn’t the type to do casual but he was also a healthy seventeen year old boy that had a mostly naked pretty girl on a bed asking for sex!</p>
            </blockquote>





	Firsts - Sam

[](http://s1345.photobucket.com/user/fanficstuff1/media/Banners/firstsparttwo_zpsac689b3e.jpg.html)

  
Sam Winchester was quite unlike his older brother. He didn’t have the same confidence Dean had with the opposite sex or with anything in general that wasn’t related to schoolwork. He knew Dean had started messing around with girls from a very young age because his older brother always had to brag about his conquests even when Sam was still very young and the thought of kissing girls let alone anything else just grossed him out. He even knew when Dean had lost his virginity because, to ten year old Sam’s horror, he’d lost it in Sam’s bed while he was at a sleepover.

Sam’s first kiss was with a girl in his class named Stephanie and after that very chaste peck on the lips she told all of her friends at McKinley that he was her boyfriend. He thought that was pretty cool even though she kinda scared him sometimes. Stephanie had just turned twelve and was always touching him and Sam at eleven didn’t quite know what, if anything, he was supposed to do with that. To his horror, she had even grabbed his thigh under the table when he was eating Thanksgiving dinner with her family right under the noses of her mom and dad. Before they had left town, he and Stephanie kissed a few times (no tongue because that was just eeuw) and she put her hand on his crotch. He ran almost all the way home after that with his heart hammering in his chest and his pre-pubescent dick hard in his pants.

Sam’s first proper kiss didn’t happen until he was fifteen. She was pretty and smart and just as Sam’s luck would have it – and this was something that would repeat itself on and off even throughout his adult life – she was one of the monsters they were trained to hunt and kill. Her name was Amy and she was a Kitsune. Amy knew what it was like to have to move around and not fit in and she was the first person who told him that being a freak made him more interesting and in her he saw a kindred spirit. When her mother found him in their house and tried to kill him, Amy saved his life by stabbing her own mom to death. When she asked Sam to run away to make a new life together a small part of him wanted to because he was so sick of the hunting life – sick of his father dragging him and Dean all over the country and sick of the fear that one day his brother or his father would end up dead – but he couldn’t do it. He couldn’t leave Dean. Even though Amy wasn’t human it didn’t stop him from replaying that delicious kiss over and over and wondering if she was safe wherever it was she had run to.

As traumatic as the circumstances surrounding that first kiss were it had opened up Sam’s confidence a little. Now he knew how good kissing could be he wanted to do it again...and again.

The first girl to let him do more than kiss was Monica Richardson. They had been living in Kenosha for four months – a long time by Winchester standards – and he had actually made some pretty good friends. Both he and Monica were fifteen and spent much of their time in the library. She had a shy smile, a honey blonde bob and glasses that kept sliding down her cute little freckled nose. It took him two weeks to build up the courage to ask her to go get a soda with him after school and another week to kiss her. What Dean had told him about how ‘it's the quiet ones that'll surprise you' seemed to apply to Monica. After he worked up the nerve to kiss her, Monica couldn’t keep her hands off him. He'd go to her house after school to study but most of the time it ended up being long make-out sessions and very little actual studying. Monica gave him his first hand-job and she let him touch her too. Sam was heartbroken when they left town because he thought he maybe loved Monica a little. He hated his dad for making them leave and after that he and his dad went from butting heads to fighting constantly.

Sam's first blow job wasn't even from a girl. He and Rick Mason were on the soccer team together and when Rick had asked Sam to tutor him in algebra he really hadn’t thought it was anything other than the boy needing help with math. Rick was tall and lean with dark blonde hair, bright blue eyes and a killer smile and Sam thought he was cute which had really confused him. He'd never had a crush on a boy before (other than his hero-worship of Dean) and he hadn’t been sure he was normal. In fact, he was pretty sure he had never been normal. He had nobody to ask about these things because there was no way in hell he was ever going to tell Dean that he thought he might be into guys as well as girls. Most people in the schools he went to already called him a freak, he would never take the risk that the person he loved more than anyone in the whole world would think he was as well. He knew that his brother wasn't homophobic but he wasn’t sure Dean might be so open if he found out his little brother might be bisexual.

The first time he went to Rick’s to tutor him, the boy told him straight out that he thought Sam was hot and that he was pretty sure Sam felt the same way about him. As he walked across the room toward Sam he said he’d seen the way Sam had looked at him in the locker room after soccer practice, then he stepped into Sam’s personal space and pressed his hand to Sam’s crotch. When Sam whined at the contact, Rick had wasted no time dropping to his knees making all the blood from Sam’s brain go rushing to his rapidly hardening erection which the boy licked from root to tip. When Rick closed his mouth over the swollen cock and began to suck in earnest, Sam's brain had almost short-circuited, and the only thought in his head before his brain melted and he came was _blow jobs are absolutely, positively, the most amazing thing in the entire universe!_

He and Rick traded secret kisses and blow jobs for the next two weeks until his dad had moved them again. He was sixteen years old and it seemed he had no issue with playing for both teams because apart from the awesome blow jobs, he'd really liked Rick a lot. He had wondered for a little while afterward if the reason he’d initially been attracted to Rick was because he’d kind of reminded Sam of Dean – with the same bigger than life, cocky personality. He wondered if maybe his fucked up teenage hormones had misplaced his hero-worshiping crush on his brother into a sexual crush on someone like him.

Sam didn’t lose his virginity until he was seventeen, something his older brother endlessly ragged on him about. He’d had ample opportunities but it just didn’t sit well with him to have sex with someone he barely knew. He wasn’t a love ‘em and leave ‘em kind of guy like Dean – it had to mean something. He wasn’t in love with Emily Burton but there was no doubt whatsoever how much he cared for her – she was really something special. It seemed all he ever did was fight with his dad and whenever he got the chance he took refuge from the bitter words with Emily and at school they spent every moment they weren't in class, together. They’d been dating for almost two months and Sam knew she wanted to take things to the next level but it bothered him that they would be moving on in the next month or so. He knew Emily was a virgin too and it didn’t feel right to take what she was offering knowing that he would have to leave her. It just wasn’t fair. He thought he and Emily could have maybe had a chance at a future if he could only stay. He may have loved his father but sometimes he hated him so damn much for dragging him along on his miserable quest for vengeance.

Even though he could never tell Emily anything close to the real reason the Winchesters moved from place to place, he did tell her how much he hated his family's nomadic lifestyle and she had been helping him with applications for scholarships so that he could go to college – be normal, live a normal life. The night Sam lost his virginity he and John had had the mother of all screaming matches. He’d missed an significant test because he’d been dragged along on a weekend hunt which was supposed to be only two days tops but they didn't get back until Tuesday. It was a test that could affect his grades which in turn could affect his scholarship chances. After both he and his father had yelled themselves hoarse his dad had fallen asleep at the bottom of yet another bottle of whiskey and Dean had gone out to a bar muttering something about being sick of listening to the fighting and why was it Sam always had to goad their dad at every turn. Sam went out through his bedroom window. It never seemed to matter to his father or brother that school was important to him. It made him more determined to continue to get good enough grades so he could escape a life of hunting.

He tapped on Emily’s window and she had no problem letting him in. Her parents were asleep at the opposite end of the house and although they had to be quiet, they didn’t need to be silent. She listened as he poured out his anger and frustration and then kissed him until he was breathless.

“You can stay here tonight as long as you're out before my parents get up. They won’t be awake before seven.”

“You want me to stay all night?”

“Do you really want to go home?”

“No, I’m already going to get my ass kicked when I go home but I don’t want to get you into any trouble.”

Emily looked at him and smiled and then lit a couple of candles on her bedside table and turned off the lamp.

“I really want you to stay with me, Sam," she leaned in and kissed him again, "I want...” She sat up and nervously pulled her nightgown over her head leaving her naked except for her panties. Sam’s breath caught in his throat and after sweeping his hazel eyes over the expanse of her flesh he raised them to meet her chocolate colored eyes. She looked almost ethereal with her dark hair and pale skin that almost glowed in the low flickering light. She looked so beautiful.

“Em, what are you...are you really sure?”

“Yeah, c’mon, take these off,” she said as she started to unbutton his jeans, “I want you to make love to me, Sam.”

He felt almost lightheaded, they were going to have sex. It was going to happen. It was really going to happen!

“I want us to be each other's first. I know you said you’ll be moving again soon and I wish you weren’t but at least we can have this. I want this, Sam. I want you.”

Lust and nerves were duelling their way through his consciousness, each taking turns at getting the upper hand. Sam wasn’t very experienced because he wasn’t the type to do casual but he was also a healthy seventeen year old boy that had a mostly naked pretty girl on a bed asking for sex! He was so hard it was almost painful and so on edge he knew he wouldn’t last long. Then he realised something that made disappointment override everything else.

“Damn it. I don’t...um...have anything with me...I left my wallet at home.”

“It doesn't matter.”

With the words Dean had pounded into his brain from the time he was thirteen – _no glove, no love_ – rattling around in his head he knew he could never go through with it. They may be virgins and disease free but there was no way he was ready to be a father. Just the thought of that was making his erection wilt. He sighed and shook his head.

“No Sam, you dumbass.” She rolled her eyes and looked at him with fond exasperation, “I have condoms. I bought them after the first time we talked about maybe doing this.”

She dug around in the bottom of her underwear drawer and took out two boxes of Trojan Magnums. “One of these better be the right size. Do you know how embarrassing it was to buy these?” She looked up through her lashes and giggled. “I don’t know much about how they’re sized but I know you’re a big boy.” They may not have had full-on sex before but there had been some serious petting sessions.

Sam flushed a deep red, picked up the box of XLs and said sheepishly, “These ones.” He opened the box and placed a condom on the nightstand. “Are you really sure?”

She grabbed both of Sam’s large hands and placed them on her breasts and Sam let out a soft moan. She leaned forward until their lips were just touching and whispered, “I’m a little scared but I’m really sure.”

Sam pulled her in close with one arm around her waist and he cradled her head in his hand he pressed her down onto the bed and kissed her, biting lightly on her bottom lip and then soothing it with his tongue. He began to kiss down her neck as he ran a hand up her thigh to the firm globe of her ass and then between her legs. He slipped his long fingers in under the elastic of her panties finding her already slick and they both moaned simultaneously when he slid his fingers over the wet warmth of her.

He kissed and licked down to her breast and swirled his tongue around the hard bud of her nipple eliciting a sigh which turned into a whimper as he grazed her clit with his thumb. Although they had done things numerous times before, both of them had been mostly clothed and now with the wonderful sounds she was making and the feel of her naked body against his, Sam was ridiculously close to losing it. He moved back up to kiss her as he circled her clit with his thumb and slid a finger inside of her. She writhed underneath him, hard nipples grazing his chest and her thigh giving constant friction to his aching cock. When she plunged her hand into his boxers, barely wrapping her hand around his length, his orgasm hit him like a freight train and he cried out softly as he spilled into her hand and onto her thigh.

When he came down from the high of coming so hard, he was mortified. They still had their underwear on, hadn’t even gotten to the good part and he’d come as fast as he had when he’d gotten his first handjob _and_ he’d come before Emily. _This would never happen to Dean!_

“I’m so sorry.” He had his face buried against her neck and was too embarrassed to look at her. 

“Hey, it’s okay.” 

“God, I’m such a loser. It’s just...you’re so beautiful ...and you feel so good and...” 

“Shh, it really is okay. You think I’m beautiful?” 

He raised his head then and looked her in the eye still blushing deeply. “God, yeah,” he breathed. “Emmi, you’re gorgeous.” 

She beamed at him and he couldn’t help but smile back, full dimples on display. He was still embarrassed but when she looked at him like that, with such happiness and adoration, things didn't seem so bad after all. 

Emily scooted over to the edge of the bed and reached over to grab a towel that was hanging on the back of a chair and wiped off her hand and her leg then gave the towel to Sam. She playfully tugged at the elastic on his boxers until he lifted his hips and she slipped them off him and threw them to the floor followed quickly by her own panties. She pulled him back toward her, wrapped her arms around his neck and whispered in his ear, “Now where were we?” 

He’d always known she was great but he couldn’t believe how cool she was being. He didn’t expect her to laugh but he had expected her to look disappointed. Instead, she looked...well...pleased. He rolled her onto her back and kissed her languidly. He had to admit that now the urgency was gone it was actually better. He was relieved he could take more time to make it as good for Emily as he could. He was pretty nervous about it being her first time, knowing he was larger than average even when he wasn’t hard. He’d been given the nickname ‘tripod’ by some of the guys in his gym class who had seen him in the showers at his last school which had embarrassed the hell out of him when it spread through the small school like wildfire. And to his utter humiliation, the name had somehow even gotten back to Dean who had spent weeks teasing him mercilessly by bringing it up in the most inappropriate places just to watch him squirm and blush. 

He kissed his way down Emily’s body stopping to suckle at her nipples while he teased and stroked up her inner thighs without actually touching where she wanted him to be. He continued covering her torso and stomach with open mouth kisses, circling his tongue around her navel before lightly blowing over the damp thatch of curls between her legs. 

“Please, Sam.” 

She sounded so wanton and he felt his cock starting to thicken again when she parted her legs allowing him to settle between them. With the first touch of his tongue to her clit she let out a delicious moan and grabbed at his hair. He loved this. He absolutely loved going down on her and making her quiver. He loved her scent and her taste and the pretty noises she made when she was nearing climax. Of all of the things that they had done so far this was his favourite although he felt that was probably going to change once he sank himself inside of her. 

He took his time sucking and licking at her clit like he was worshiping it. When he slid two fingers into her, that was all it took and he felt her body stiffen and tremble as her walls fluttered around his fingers and he moaned as lapped at the sudden gush from her orgasm. He was rock hard again as he kissed his way back up her body loving the little trembles of her aftershocks. 

“Are you ready?” 

She smiled up at him, her pupils blown so that he couldn't really see the brown anymore and nodded, “Just...um...just go slow okay.” 

“You can tell me to stop and I will. I don’t want to hurt you.” 

“It’s going to hurt, Sam, but I still want this.” 

His nerves were back in full force again as he reached over and picked up the condom wrapper and his hands shook so much he dropped it twice. Emily took the little packet and tore it open and gave the condom to him. He was so nervous he had trouble rolling it on and he would have laughed if it wasn’t for the fact that he was both incredibly horny and totally terrified. 

When he settled himself above her, he kissed both of her eyelids and then her nose. He thought he should tell her that he loved her but those were words he knew he could never use unless he really meant them. He liked her so very much so instead he said, “You’re so beautiful, Emmi” and she leaned up to kiss him. When he broke the kiss he lined himself up and gently started to push his way inside. He had to grab the base of his cock to stave off coming at the first feeling of that incredibly tight warmth. He had to fight to keep his eyes open as he was overwhelmed by the sensation of feeling himself slowly pushing in because he needed to see if he was hurting her. He felt resistance and Emily’s breaths were coming in short pants, her brow furrowed from the discomfort. 

Jesus, he was close to coming. The tightness of her was overpowering but when he felt a sudden give and Emily cried out softly from pain, dug her fingernails into his back and screwed up her face it brought him back from the brink quickly. He stilled even though the urge to push was monumentally strong. “God, Em, are you...should I stop?” 

A tear fell from the corner of one of her tightly closed eyes and she shook her head and replied, “Just give me a sec, I’m okay.” She pulled in a deep breath, opened her eyes and saw Sam’s hazel eyes looking at her with such worry she smiled and then urged him to move. As he pressed in as far as she could take him he was torn between concern that he had hurt her and the delicious feeling of God _yes_ so _fucking_ good. She couldn’t take his full length but it didn’t matter because being inside of her felt so amazing. He pulled back and pushed in again slowly finding his rhythm and then kissed her deeply, their tongues tangling as she started to match his thrusts with presses of her hips. He could tell she was still uncomfortable so he reached his hand between them and began to rub her clit soft and fast. He raised his head and bit his lip trying desperately not to come until she did but he felt the familiar coil of heat and his balls started to tighten. He lost all rhythm and threw his head back as his orgasm ripped out of him and tried not to cry out and wake Emily's parents. 

With labored breathing he dropped forward and kissed her and, then with great difficulty, resumed his attention on her clit while fighting to hold himself above her on one very shaking elbow. She began a litany of “oh, oh, oh” and he felt her contracting around his cock as Emily came shaking beneath him. He worked her through it and then gently eased his slowly softening cock out of her holding the base of the condom tightly. 

When he disposed of the condom he wrapped himself around Emily and asked if she was okay. She answered by kissing him long and sweet. 

“Was it...did I...” 

“It was perfect, Sam. It hurt for a bit but then it felt good although I’ll probably be sore tomorrow...but good sore.” 

He winced but she smiled at him and they wrapped themselves together in a sweaty tangle of limbs and kissed until they fell asleep.  
He woke just before dawn and he kissed Emily awake and told her how much the night had meant to him. He snuck back out of her window as the sun was coming up over the horizon. When he got back home his father was waiting and he was beyond furious, launching into a tirade as soon as Sam walked in the door. Within minutes, the shouting brought Dean into the room ready to join his father at yelling at Sam for worrying them. When he saw Sam’s face it stopped him short. His stubborn, defiant little brother wasn’t yelling back and there was none of the usual fury – in fact he had kind of a dopey look on his face. 

When John stormed out of the house slamming the door in his wake and Sam went to go to his room, Dean raised an eyebrow in question. 

“What?” 

“You know you’re gonna be paying big time for staying out all night with the training from hell and any other God awful punishment dad can think up for the foreseeable future.” 

Sam sighed and then shrugged, “Yeah, I know.” 

“So was it worth it?” Dean asked with a smirk. 

Sam smiled sheepishly,“Yeah, it really was.” 

Dean threw his arm around his not so little brother’s neck and pulled him down for a noogie. 

“Aw, our little boy’s all grown up.” 

“Shut up.” Sam blushed furiously but couldn’t keep the grin off his face. 

“Go take a shower, princess. Dad's gonna be back with the punishment from hell as soon as he's calmed down and because I’m such an awesome big brother, I’ll take you out for breakfast to celebrate your deflowering before he kills you.” 

Sam rolled his eyes and flipped Dean the finger, smiling all the way as he walked out of the room. When he was in the shower Dean snuck into the bathroom and said, “Hurry up, bitch,” as he flushed the toilet. He ran out of the room laughing as Sam screeched, “Oh, you jerk!” when he was hit by ice cold water. 

_Fin_


End file.
